By Fiona Good-Sirota By Fiona Good-Sirota | January 14, 2025 | Food & Drink, Lifestyle, Feature, Features, Featured, Food & Drink, Guides,
S’mores fondue, seasonal cocktails and fire pit seating at The Gwen’s Winter Curl & Chill
As bone-chilling temps return to the Windy City, these local establishments are turning up the heat with an array of seasonal experiences. From an après ski-inspired cocktail pop-up to hot tub boat rides along the Chicago River, we’ve rounded up the best things to do this winter in Chicago.
521 N. Rush St. / Website
Round up your nearest and dearest and immerse yourself in a winter wonderland experience at luxury travel destination The Gwen. The hotel is ringing in the season with The Gwen’s Winter Curl & Chill experience on the rooftop terrace, featuring a curling rink, cozy fire pit seating, tasty treats like the spot’s Lux S’mores Fondue and themed cocktails like boozy hot chocolates, mulled wine, eggnog flights and more. The hour-long experience is priced at $25 and is complimentary for children under six.
43 E. Ohio St. / Website
Eataly Chicago has just unveiled a luxe winter pop-up experience. Named after the Italian Alps, Alpina transports visitors to an après ski-themed winter wonderland, complete with inspired decor, new event programming, hands-on classes, workshops, Alpine-esque cuisine, warming cocktails and exclusive happy hour offers. During their visit, guests can dine on polenta bar offerings (rag di carne, ragù di funghi, salsicce e funghi, short ribs ragù, or goulash) and dig into seasonal staples like fondue, gnocchi with black winter truffles, stuffed and breaded chicken cutlets and more. Libations include wines from Italy’s Northern regions, plus hot toddies, Bombardinos (Italian eggnog) and spirit-free selections.
12 S. Michigan Ave. / Website
As winter weather returns to Chicago, Cindy’s Rooftop is warming things up with its après ski-inspired hot cocktail pop-up on the South Terrace, open daily from 5 to 10 p.m. through Feb. 28. Beverage manager Kylie McCalla has curated a lineup of seasonally inspired vegan cocktails, including hot cocoa spiked with Rémy Martin 1738, spiced mulled wine, buttered rum and Westland whiskey-infused hot toddies. Relax and unwind with a festive atmosphere, scenic skyline views and comforting sips that accommodate vegan and dairy-free visitors.
230 N. Michigan Ave., Floor 24 / Website
Pendry Chicago’s rooftop bar and lounge, Chateau Carbide, is serving up seasonal sips and French-inspired small bites with its newly debuted Winter Garden menu. Stave off freezing temps with offerings like bite-sized boucheés, waffle frites with brie and caviar, French onion grilled cheese and espresso crème brulée with hazelnut praline. Level up your visit with the restaurant’s booze-infused selections, including the chocolate chaud for two with a spirit enhancement, the Blanco tequila-spiked Cranarchy and the Hot to Trot with whiskey, oolong tea, lemon, turbinado and anise. On Thursdays through Sundays from 5 to 11 p.m., visitors can opt for seating in a private lodge, complete with fireplaces, plush blankets and space for up to six guests.
See also: Fun Things To Do Indoors On A Cold Or Rainy Day In Chicago
3057 N. Rockwell St. / Website
Gather six members of your crew and embark on a scenic journey along the Chicago River as you take in panoramic skyline views from one of Chicago Boat Company’s one-of-a-kind hot tub boats. For the second year in a row, the rental service is offering 90-minute rides that cruise eastward toward Michigan Avenue or westward to Wells Street, complete with a Bluetooth speaker, floating cup holders, a waterproof phone case and more. For groups of up to 12 guests, the company’s fully enclosed and heated 22-foot Luxury Duffy boats are also available.
When it comes to getting out on the ice, the Windy City delivers with a variety of indoor and outdoor rinks—perfect for brushing up on your skating skills. Whether you opt to take in the skyline views at McCormick Tribune Ice Rink or immerse yourself in a rooftop winter wonderland at The Peninsula Sky Rink, these ice skating spots are ideal for visitors of all ages and skill levels.
Read the full list here.
820 W. Fulton St. / Website
French-American eatery Bar La Rue is ushering in the season with a ski chalet-inspired atmosphere, exclusive bites, themed cocktails and cozy fire pit patio seating. Visit on weekdays from 4 to 6 p.m. to enjoy a winter happy hour menu with highlights like cheese fondue service for $20, bottomless frites for $10, oysters priced at $2 each and bubbles by the glass, available on weekdays from 4 to 6 p.m. Visitors can also warm up with hot libations like the L’Orange Blossom (vodka, Domaine de canton, orange blossom and lemon), the Jean Claude (bourbon, benedictine, blackberry, mint and lemon) and spicy mulled wine.
Looking for more luxe stops in the city? Check out our guide to The 8 Best Chicago Fireplace Bars & Restaurants.
Photography by: Photography of The Gwen’s Winter Curl & Chill by Gene Yoon; photography of the Après Ski-Inspired Pop-Up at Cindy’s Rooftop courtesy of the Chicago Athletic Association